Thanks, I just tried with the Try_TLS entry, but unfortunately no luck. But it was definitely a good idea to try! Not really finding anything useful in trace: mailer 3 (cyrusv2), host `' user `cyrus', ruser `<null>' state=OK, next=0x0, alias 0x0, uid 0, gid 0 flags=*80100182*<QPRIMARY,QPINGONFAILURE,QPINGONDELAY,QSECURE,QRCPTOK> owner=(none), home="(none)", fullname="(none)" orcpt="(none)", statmta=(none), status=(none) openmailer: TCP imap.example.com lmtps openmailer: MCI@0x55bef1997ab8: flags=4<CACHED>, errno=104, herrno=0, exitstat=75, state=0, pid=0, maxsize=0, phase=client LHLO, mailer=cyrusv2, status=4.4.2, rstatus=(null), Flags 0x80100182 & 0x0100000 is "STARTTLS SMTP extension supported" , but I think it should be 0x0200000: "STARTTLS is active"